See all properties
Entire home

Harbor Cottage at the Chesapeake Bay - Dog Friendly Beach

Photo gallery for Harbor Cottage at the Chesapeake Bay - Dog Friendly Beach

Deck with awning and a Harbor View
Fun for kids as the water is shallow.
Living room opens onto deck; sofa unfolds to full size bed.
Dining area, opens onto deck; table expands for seating for 10!
Well equipped kitchen

Reviews

9.8 out of 10, Loved by Guests
Top 10% of guest reviews in this area
2 bedrooms2 bathroomsSleeps 592.9 sq m

Popular amenities

  • Onsite parking available
  • Dog-friendly
  • Kitchen
  • Air-conditioning
  • Outdoor barbecue
  • Deck or patio

Explore the area

View map
St Leonard, MD
  • Place, Flag Harbor Marina
    ‪3 min walk‬
  • Place, Flag Ponds Nature Park
    ‪12 min walk‬
  • Place, Matoaka Beach
    ‪15 min walk‬

Rooms & beds

2 bedrooms (sleeps 5)

Convertible bed(s)

1 Double Futon

2 bathrooms

Bathroom 1

Bathtub or shower · Toilet

Bathroom 2

Bathtub or shower · Toilet

Spaces

Deck or patio
Kitchen
Dining area

About this property

Harbor Cottage at the Chesapeake Bay - Dog Friendly Beach

Harbor Cottage. Relax on the deck overlooking the fishing and sailboats of Flag Harbor opening onto the Chesapeake Bay. Only a three minute walk to the big sand beach famous for fossils from the Miocene period. Very quiet and not crowded. Great fishing from the beach or charter a boat. Shallow water makes for great swimming for kids. Bring your well behaved dog to enjoy the beach and swimming with you.
We keep a vacant day between renters as a courtesy to our cleaners and our arriving guests. These dates are blocked on our calendar.

Washington DC or Annapolis is only one hour away, and the entire Chesapeake Bay area is steeped in American history. Just 15 minutes from the shops and restaurants of Solomons Island, and the terrific Marine Museum there. Many state and county parks for hiking. fossil hunting, and birdwatching.
PLEASE CONTACT ME BEFORE CLICKING "BOOK IT NOW"
Keywords: Vacation Rental Cottage, Beach House, dog

Add dates for prices

Have a question?

AI iconBeta

Get instant answers with AI powered search of property information and reviews.

Similar properties

The Bay is our backyard.
Our Always Dreaming Cottage - The Bay At Your Back Steps
Port Republic
  • Kitchen
  • Pet-friendly
  • Air-conditioning
  • Laundry room
9.8 out of 10, Exceptional, (141 reviews)
Our Always Dreaming Cottage - The Bay At Your Back Steps

House Rules

Check in after 3:00 PM
Minimum age to rent: 25
Check out before 11:00 AM
default

Children

Children allowed: ages 0–17
Parents are responsible for toddler-proofing
default

Events

No events allowed
Seating for 10 at the dining table. Ask me.
default

Pets

Pets allowed: dogs (limit 2 total)
Well behaved dogs are welcome. Add $35. per dog.
default

Smoking

Smoking is not permitted

Check-out instructions

The host requires you to complete the following before checking out:
Turn off the lights, lock the doors and return the keys
Please leave the cottage as tidy as you found it. Put trash in outside barrels, leave the beach pass in the kitchen, put the key back in the lock box - and thank you very, very much!
Failure to complete these may result in a negative review from the host.
Well behaved dogs only - please pad the floor under the crate to protect the hardwood floor. Contact me if your dog as ever bitten man or beast.
Our beach is unguarded - swim, fish, and boat at your own risk. Clean-up after yourself and your dog on the beach and neighborhood. No fireworks.
Stay off the cliffs - they are a landslide danger and private property. Fossil hunt at the water line or in the surf for better results and safety.

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Note from host: Seating for 10 at the dining table. Ask me.
Long-term renters welcome
Host has indicated that there are no carbon monoxide detectors or gas appliances on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock

About the area

St. Leonard

Located in St. Leonard, this cottage is near a water park and on the waterfront. Flag Harbor Marina and Perigeaux Vineyards and Winery are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural beauty can explore Chesapeake Bay and Battle Creek Cypress Swamp Sanctuary. R&J's PlayPark and Kocen Arts Center are also worth visiting. Kayaking, power boating and fishing offer great chances to get out on the surrounding water, or you can seek out an adventure with hiking nearby.
View more Cottages in St. LeonardOpens in a new window
Map
St Leonard, MD

What's nearby

  • Flag Harbor Marina - 3 min walk - 0.3 km
  • Flag Ponds Nature Park - 12 min walk - 1.1 km
  • Matoaka Beach - 15 min walk - 1.3 km
  • Calvert Cliffs State Park - 16 min drive - 17.1 km
  • Patuxent River Naval Air Station - 44 min drive - 43.7 km

Getting around

  • Ronald Reagan National Airport (DCA) - 73 min drive

Restaurants

  • ‪Linda's Produce Stand - ‬9 min drive
  • ‪Vera's White Sands Beach Club - ‬17 min drive
  • ‪Frying Pan - ‬14 min drive
  • ‪Adam's The Place For Ribs - ‬11 min drive
  • ‪The Tavern - ‬5 min drive

Frequently asked questions

Is Harbor Cottage at the Chesapeake Bay - Dog Friendly Beach pet-friendly?

Yes, this property allows dogs (limit 2 total).

How much does it cost to stay at Harbor Cottage at the Chesapeake Bay - Dog Friendly Beach?

As of 3 May 2026, prices found for a 1-night stay for 2 adults at Harbor Cottage at the Chesapeake Bay - Dog Friendly Beach on 6 July 2026 start from NZ$283, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking at Harbor Cottage at the Chesapeake Bay - Dog Friendly Beach?

On-site parking is available at the property.

What time is check-in at Harbor Cottage at the Chesapeake Bay - Dog Friendly Beach?

Check-in begins at 3:00 PM.

What time is check-out at Harbor Cottage at the Chesapeake Bay - Dog Friendly Beach?

Checkout is at 11:00 AM.

Where is Harbor Cottage at the Chesapeake Bay - Dog Friendly Beach located?

Situated on the waterfront, this cottage is steps away from Chesapeake Bay and Flag Harbor Marina. Long Beach and Northern Chesapeake Bay are also within 15 minutes.

Reviews

9.8

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 142 out of 165 reviews
Rating 8 - Good. 21 out of 165 reviews
Rating 6 - Okay. 1 out of 165 reviews
Rating 4 - Poor. 1 out of 165 reviews
Rating 2 - Terrible. 0 out of 165 reviews

9.4/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

8/10 Good

M B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great hosts and great property. The location is nearly perfect. We might have been the first guests of the season or at least when bookings are light, so there were some bumps, but things happen and the hosts made sure everything was handled as best as possible. This might our new "spring break" place! We need to practice our fossil hunting skills because we are terrible!
Stayed 4 nights in Apr 2026
Verified

10/10 Excellent

Judith B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Everything was great! The cottage was well appointed. The hosts were very welcoming, and the all the people we met on our walks were very friendly. I would definitely recommend this cottage.
Stayed 20 nights in Dec 2025
Verified

10/10 Excellent

Ed O.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Host was easy to communicate with. The place is wonderful!
Stayed 21 nights in Nov 2025
Verified

10/10 Excellent

eileen m.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Another great stay at Harbor Cottage. We stay there at least once a year and look forward to it every time. Can't beat the location, neighborhood or convenience to the private beach. The cottage is charming with a great view of Flag Harbor right across the street.
Stayed 4 nights in Oct 2025
Verified

10/10 Excellent

jason s.

Liked: Cleanliness, check-in, communication, location, listing accuracy
stay was excellent as always. great Neiborhood to enjoy beach with family and dogs. host was a pleasure to deal with. look forward to another season.
Stayed 15 nights in Sep 2025
Verified

10/10 Excellent

Pamela B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The cottage was everything as advertised and more!! We loved it so much that we could live there forever!!Katherine was awesome!!!
Our pup Winnie exhausted from exploring all day in her bed for the night.
My husband Bob enjoying the bay with Winnie.
Stayed 4 nights in Aug 2025
Verified

10/10 Excellent

Steve D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing property we loved it

I will be back next year this location was great.
Stayed 5 nights in Oct 2024
Verified

10/10 Excellent

Jeannine C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We Our stay was perfect. The cottage was spotless and had everything we needed.The beach was a minute away and the view off the porch was great. We like to birdwatch and it was fantastic in the marina. We will definitely return.
Stayed 7 nights in Sep 2025
Verified

10/10 Excellent

Coleby M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Quiet Chesapeake Getaway

Cozy spot on bay. Great for beach hikes and birdwatching.
Stayed 4 nights in May 2025
Verified

10/10 Excellent

Nick G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great location

My mother loved the harbor and beach that was right there.
Stayed 7 nights in Oct 2024
Verified

10/10 Excellent

edith f.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Everything was just as listed. Beautiful house and neighborhood.
Stayed 4 nights in Sep 2025
Verified

10/10 Excellent

Gloria V.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect beachside retreat

This house was the perfect fit for our stay in st Leonard. The kitchen was well appointed and the facility was very comfortable. We would definitely stay here again.
Stayed 4 nights in Nov 2024
Verified

10/10 Excellent

Amy N.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Lovely Home Near the Beach

House had everything we could have asked for, well stocked kitchen and lots of great information on local attractions available! Very nice location, great value!
Stayed 4 nights in Jun 2023
Verified

10/10 Excellent

Judy O.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful location w easy access to beach for fishing and shelling ! Cottage very clean and comfortable w a new kitchen , large dining table and big deck ! Stores and restaurants not far but beware they are closed on Mondays except fast food ! Very welcoming community A-big thank you to the owner the O’s
Stayed 4 nights in Aug 2025
Verified

10/10 Excellent

Ellen R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Family Get-Away

This was our 3rd summer visit to this home. We love it and will visit again!
Stayed 6 nights in Aug 2023
Verified

10/10 Excellent

eileen m.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Love Staying at Harbor Cottage

Another great stay. The location and charm of Harbor Cottage can't be beat if you are going to the Calvert Cliffs area! Katherine is a wonderful host.
Stayed 4 nights in Sep 2023
Verified

10/10 Excellent

eileen m.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Another Wonderful Stay at Harbor Cottage!

Had a great time. Many thanks to our hosts.
Stayed 4 nights in Apr 2023
Verified

10/10 Excellent

Steve M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Calvert Cliff's Refuel

Stayed here for about 3 weeks for a short term work assignment, very clean and pretty well stocked. No issues, I'd stay again.
Stayed 20 nights in Feb 2025
Verified

10/10 Excellent

marie w.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Location, location, location! A wonderful stay at the Harbor cottage. Beautiful view inside the home of the harbor and having a beach, almost to yourself, a mere block away was priceless. Peaceful. Restful. Very comfortable home with most needed provisions. One hour to Washington DC also so can enjoy the city as well. Enjoyed my stay with my husband and two small pups very much.
Stayed 7 nights in Aug 2025
Verified

10/10 Excellent

Virginia M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Harbor Cottage is located in a quiet neighborhood within walking distance to a private beach on the Chesapeake Bay. Lovely views of the marina from the deck and inside house. If you like to cook it has a spacious kitchen. The owner was very responsive to questions. We will definitely rent this property again.
Stayed 5 nights in Jun 2025
Archival

10/10 Excellent

susanne f.

Perfect cozy cottage!!! We loved our stay!

Everything about our experience was perfect- from the reservation to check out. Katherine was very hospitable! The cottage was perfect for our family gathering- clean and comfy beds were also a plus 👍🏻Can’t wait until our next visit!!
Stayed 4 nights in Dec 2017
Verified

10/10 Excellent

Verified traveller

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great little cottage!

We had a wonderful stay at harbor cottage! It was very clean and comfortable. The area is fantastic if you’re looking for someplace to chill and relax. Very dog friendly!
Stayed 4 nights in Apr 2023
Verified

10/10 Excellent

Allison H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Lovely

We really enjoyed our stay!the home had everything we needed! Such a memorable stay, Thank you 😊
Stayed 4 nights in Jul 2023
Verified

10/10 Excellent

Brian N.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Return trip, great location and property.

This is our second stay, and had a great time on the beach! The house is fully equipped with everything you need and is comfortable. We had a great time and will be back next year!
Stayed 4 nights in May 2023
Verified

10/10 Excellent

Suzi S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Lovely

I really enjoyed the area and property
Stayed 7 nights in Aug 2024

About the host

Hosted by Katherine Nelson

Host profile image
We love this area for a quick get-a-way: our neighbors are friendly and helpful, and the beach is peaceful and beautiful! We enjoy watching the eagles and ospreys fish, and the large schools of fish that can be seen in the (usually) clear water.

Why they chose this property

We found this peaceful and friendly spot by chance - it's so close to the Washington DC area. The community is very dog-friendly, and when we are alone on the beach, they can romp in the waves off the leash. There aren't dangerous tides, and seldom rough water.

What makes this property unique

We have discovered the fun of fossil hunting, or just sitting at the beach and reading and re-charging our energies. The light, wind, and water are constantly changing. You can walk the beach for hours.

Languages:

English

Premier Host

They consistently provide great experiences for their guests
Tell us how we can improve our siteShare feedback